According to the American Film Institute, this is the greatest American comedy ever made. I would have to agree with that. Mostly for the punch line and more so for Jack Lemmon's reaction to it.
Set in 1929's Chicago during the days of prohibition, jazz and gangsters, Tony Curtis and Jack Lemmon play struggling musicians Joe and Jerry. They witness the Saint Valentine's Massacre and are seen by "Spats" Colombo (George Raft who was a close friend to several gangsters) and flee for their lives. Dressing up as Josephine and Daphne, they join an all-girls band which is headed to Florida where they meet Marilyn, who plays Sugar the band's singer. Joe does an impression of Cary Grant in order to romance Sugar as a millionaire with a yacht and Daphne is romance by Osgood Fielding III (Joe E. Brown). But then Spats and his gang turn up in Florida for a mob convention and all hell breaks loose.
The film isn't strictly historically accurate, but who cares. This is a Billy Wilder comedy at it's best!
Another thing I love about this film is that you can tell that Tony Curtis is really playing the sax.
"Look how she moves. It's like Jell-O on springs."
"Just keep telling yourself: you're a girl!"
This is actually the Hotel Del Coronado in southern California, which you can still stay in today.
"We named the oil company after them"
Don't you think that for 1959 this dress is terribly daring, even shocking? Actually the whole movie is rather shocking for 1959. You have the romance between Osgood and Daphne, Sugar has stated that she's lived with a few saxophone players, Joe is a womanizer and then you have this dress which doesn't leave anything to the imagination. Some Like It Hot didn't receive approval for the Production Code and was condemned by the League of Decency and was one of the films that contributed to the end of the Code. This is another excellent reason to watch this film.
"Congratulations, who's the lucky girl?"
Best punchline ever! Mostly for the look on Jack Lemmon's face.